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Pyridine → 5-Benzoylamino-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamide

HRID 421081
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 421081
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)=[O:8].N1C=CC=CC=1.O1CCCC1.[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O>[C:37]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)=[O:8])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
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Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 10406441HCID 10406441, Verbindung

Produkt 1

HCID 100502785-Benzoylamino-N-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxybenzamideAusbeute 25,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

Under argon atmosphere, a mixture of 5-amino-N-[3,5-bis(trifluoromethyl)-phenyl]-2-hydroxybenzamide (364 mg, 1 mmol), pyridine (95 mg, 1.2 mmol) and tetrahydrofuran (10 mL) was cooled on ice. Benzoyl chloride (155 mg, 1.1 mmol) was added, and the mixture was stirred for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (121 mg, 25.7%) as a white solid.

Aufarbeitung

  1. temperaturewas cooled on ice
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-b92b0287276d4167a5fbac328e15c496
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08097759B2

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